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In short, this trope is about "dressing in the clothing of the opposite sex." The long version can get a little more complicated.

Crossdressers may be men dressing as women, or women dressing as men. Contrary to popular belief, crossdressing does not necessarily imply homosexuality. An element of sexual arousal ("transvestic fetishism") may be involved in dressing, but not necessarily. And sometimes the primary purpose for crossdressing is simply disguise. This supertrope covers all the various possibilities and permutations.

Distinguished from Drag Queen, which tends to be strongly associated with gay men and has an inherent aspect of "performance." Also not to be confused with transgender, which describes people who identify as a different gender from that which they were assigned at birth. There's always potential for overlap, however. A drag queen may also dress as a woman while "offstage", and thus be a crossdresser as well. Some people may start out as "merely" crossdressers, only to eventually discover that they are transgender.

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"Crossdresser" and "transvestite" aren't necessarily synonymous in Real Life. Many different (and often contradictory) definitions for each term can be found. This trope is intended to encompass all of them — at least for purposes of troping. (It's also worth noting that the term "transvestite" is largely considered obsolete and pejorative nowadays.)

Note that, since the 1960s or so in western culture, there tends to be little or no social stigma attached to women wearing "traditionally male" clothing. Once upon a time, however, a woman dressing like a man (e.g., wearing trousers) would be frowned upon, or even illegal in some jurisdictions.

Boss from Hamtaro (yes, that's right, HAMTARO) does this occasionally in the Japanese series. Originally he only did it when acting as the "nurse chief" of the Ham-Ham Nurse Team (though none of the other boys were part of it, so it's unknown why Bijou wouldn't have been the nurse chief), but later on he seems more than eager to cross-dress for other reasons, including: pretending to be a girl to attract Flora's presumed husband so she wouldn't have to marry him (it turned out that the male monkey Pepe was to marry a female monkey, and Flora wasn't getting married, but still), dressing like a girl for Sparkle's show, and dressing as a female ninja in the final Nin-Ham episode (complete with makeup, which is strange since he always dressed as a male ninja previously).

Kei Shimura of High School Ninja Girl, Otonashi-san doesn't crossdress out of any desire to be seen as female, nor with any true villainous intent. He only does it because femininity is the only area in which he can surpass his rival, the title character Fuka Otonashi.

Jessie and James, members of Team Rocket from Pokémon were shown to cross dress frequently whenever they go in disguise with Jessie sometimes dressing up as a man and James dressing up as a woman. James in particular has cross dressed way more than Jessie has as he dressed himself up as a schoolgirl, a ballerina, and even went as far as buying fake breasts and entering into a beauty pageant with them, which caused an episode of the series to get banned because of him. This characteristic died down as the series progressed.

City Hunter: Ryo crossdressed a few times, usually to disguise himself (he can even make his Gag Penis disappear if someone checks his gender!) but, one time, he was trying to not be outed as City Hunter and faked having a job in a gay pub...

Kazuya Shiranami of Galaxy Angel is stated as having been forced to crossdress before he joined the Rune Angel Wing. In the first game of the Galaxy Angel II trilogy, in what becomes Natsume Izayoi's route, he finds himself forced into it once more, as a maid with Grade A Zettai Ryouiki. This situation piques the curiosity of Anise Azeat when she sees him (as both Kazuya and the crossdressed Katherine, on separate occasions) sneaking around; it's in a scene where the female Angels are undressing that Lily finally busts him.

In the third game of the Galaxy Angel II trilogy this nearly happens to Kazuya again (again in Natsume's route, here affecting Kazuya whereas the tomboyish Anise is the one affected in her route), but Lily quickly neutralizes the cause to protect Kazuya's so-called secret.

Khaos Omega is known to implement scenarios that involve crossdressing, one of them a tweaked case of Kazuya's crossdressing in the first game of the Galaxy Angel II trilogy. Here, the tweak is that Lily tries a longer-range approach to remove Kazuya's maid attire but botches it; a far bustier Anise, who had seen it coming, convinces Kazuya to resume crossdressing, which he does more passionately. Anise herself is later revealed to be the primary Alpha of a massive harem whose leader, Jet Brazie, has a special gender status allowing him to crossdress without it being identified as such (he doesn't go fully until 2550 following the capture of Tracy Dennis), which Kazuya (his role in triggering Anise and Jet's marriage without an actual wedding, due to buying Anise her Fairytale Wedding Dress), Jace Davies (a transformation-induced Chaos Reaction near his own Anise), and Jayden Omega (a sixth birthday present) also obtain.

Literature

Nevada: One of the characters in the book is convinced he's just this and not a trans woman.

Live Action TV

British television has a proud tradition of men dressing as women for comedy. It probably goes back to how men (or boys) played female roles in Shakespeare's day; re-enforced by their tradition of single-sex schools (few plays have all-male or all-female casts, so if a single-sex school has a drama program AT ALL, SOMEBODY will get cross-cast.) Some have gone so far as to say that there is nothing funnier to a British audience than a man dressed up like a woman.

Monty Python's Flying Circus did this in every episode. It probably helped that the troupe didn't usually have any women anyway (apart from Carol Cleveland), so at least some of the crossdressing was actually pretty necessary.

Night and Day's Fiona Brake and Dennis Doyle both have forays into cross-dressing; Fiona in a bid to seduce her gay husband, and Dennis because he briefly thinks he might be intersex. Also, in in the final episode, set four years into the future, we learn that Ryan Harper now wears womens clothes and goes by the name of Beverly.

Father Brown: The Victim of the Week in "The Missing Man". His crossdressing actually leads to his demise, as the person who shoots him does not recognise him in drag, and shoots him thinking he is a female intruder.

Mash: Corporal Klinger, in attempt to prove that he is clinically insane and therefore unfit for active duty, regularly shows up in some form of women's dress, right down to the earrings and slip. Unfortunately, he can't pull off "crazy" because his personality is still the same.

Video Games

Valkyria Chronicles 4: Handled in a refreshingly tasteful manner for a Japanese game. The specific details of Rosetta's gender and sexuality are not clear, but it is clear that she considers her feminine attire to be cross dressing. This is not played for laughs or even mentioned at all - nobody in Squad E seems to care one way or another.

RWBY: In Season 2, Jaune talks with his teammate Pyrrha about the upcoming dance and is utterly stunned at the idea that an amazing girl like her wouldn't get a datenote It's clear that she wants him to ask her, but he doesn't get it and she's helping him try to ask Weiss, saying that if she doesn't, he'll wear a dress. When the dance rolls around, Pyrrha indeed shows up dateless, and Jaune (who came in a tux) leaves for a minute before returning in a white dress and asking her to dance. To his credit, he doesn't show any embarrassment at all and even ends up doing a dance routine with the rest of Team JNPR.

Never shown but there are a few jokes in The Weekenders that imply Carter crossdresses.

King of the Hill episode "The Peggy Horror Picture Show" has Peggy befriending a woman named Caroline who makes her feel better about being less than perfectly feminine. However, she turns out to be a crossdresser and Peggy's self-esteem drops even lower than before when she finds out. By the end of the episode, Caroline mends fences by explaining that people like her admire women like Peggy who are strong, confident, and not afraid to be themselves.

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